JP6159025B2 - フリーラジカル重合性エチレン性不飽和ポロキサマーおよびポロキサミンの合成 - Google Patents
フリーラジカル重合性エチレン性不飽和ポロキサマーおよびポロキサミンの合成 Download PDFInfo
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- JP6159025B2 JP6159025B2 JP2016521543A JP2016521543A JP6159025B2 JP 6159025 B2 JP6159025 B2 JP 6159025B2 JP 2016521543 A JP2016521543 A JP 2016521543A JP 2016521543 A JP2016521543 A JP 2016521543A JP 6159025 B2 JP6159025 B2 JP 6159025B2
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- poloxamer
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- 229920001983 poloxamer Polymers 0.000 title claims description 55
- 229920001987 poloxamine Polymers 0.000 title claims description 26
- 230000015572 biosynthetic process Effects 0.000 title description 30
- 238000003786 synthesis reaction Methods 0.000 title description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 156
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 91
- 239000003112 inhibitor Substances 0.000 claims description 57
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 54
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 50
- 229960000502 poloxamer Drugs 0.000 claims description 37
- 150000003254 radicals Chemical class 0.000 claims description 31
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical group CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 150000007530 organic bases Chemical class 0.000 claims description 10
- -1 poloxamer compound Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 162
- 238000003756 stirring Methods 0.000 description 106
- 238000006243 chemical reaction Methods 0.000 description 98
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 81
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 68
- 239000000706 filtrate Substances 0.000 description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- 229910001873 dinitrogen Inorganic materials 0.000 description 47
- 238000004128 high performance liquid chromatography Methods 0.000 description 42
- 238000004364 calculation method Methods 0.000 description 41
- 239000000047 product Substances 0.000 description 37
- 229920001992 poloxamer 407 Polymers 0.000 description 36
- 150000003839 salts Chemical class 0.000 description 26
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 229920005989 resin Polymers 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 238000012805 post-processing Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 18
- 229920001400 block copolymer Polymers 0.000 description 16
- 239000012535 impurity Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 229950000688 phenothiazine Drugs 0.000 description 12
- 229940044476 poloxamer 407 Drugs 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- RDQSIADLBQFVMY-UHFFFAOYSA-N 2,6-Di-tert-butylbenzoquinone Chemical compound CC(C)(C)C1=CC(=O)C=C(C(C)(C)C)C1=O RDQSIADLBQFVMY-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007974 sodium acetate buffer Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- VEDXDZRQOYXKTL-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)ethylidene]cyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1 VEDXDZRQOYXKTL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920002359 Tetronic® Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910002056 binary alloy Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000013542 high molecular weight contaminant Substances 0.000 description 2
- 229920013746 hydrophilic polyethylene oxide Polymers 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- JJQCWPWUHZFKBN-UHFFFAOYSA-N CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C Chemical compound CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C JJQCWPWUHZFKBN-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-O CC(C)(C)c1cc(C)cc(C(C)(C)C)c1[OH2+] Chemical compound CC(C)(C)c1cc(C)cc(C(C)(C)C)c1[OH2+] NLZUEZXRPGMBCV-UHFFFAOYSA-O 0.000 description 1
- QNGJMQPOCSSRGI-UHFFFAOYSA-N CC(C)C(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C Chemical compound CC(C)C(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C QNGJMQPOCSSRGI-UHFFFAOYSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 229920002415 Pluronic P-123 Polymers 0.000 description 1
- 229920002012 Pluronic® F 38 Polymers 0.000 description 1
- 229920002023 Pluronic® F 87 Polymers 0.000 description 1
- 229920002065 Pluronic® P 105 Polymers 0.000 description 1
- 229920000463 Poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000010065 bacterial adhesion Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940125436 dual inhibitor Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000010069 protein adhesion Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361836471P | 2013-06-18 | 2013-06-18 | |
| US61/836,471 | 2013-06-18 | ||
| PCT/US2014/042951 WO2014205084A1 (en) | 2013-06-18 | 2014-06-18 | Synthesis of free radical polmerizable ethylenically unsaturated poloxamers and poloxamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016524014A JP2016524014A (ja) | 2016-08-12 |
| JP6159025B2 true JP6159025B2 (ja) | 2017-07-05 |
Family
ID=51168448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016521543A Active JP6159025B2 (ja) | 2013-06-18 | 2014-06-18 | フリーラジカル重合性エチレン性不飽和ポロキサマーおよびポロキサミンの合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9309357B2 (ko) |
| EP (1) | EP3010946B1 (ko) |
| JP (1) | JP6159025B2 (ko) |
| KR (1) | KR101767852B1 (ko) |
| CN (1) | CN105308080B (ko) |
| AU (1) | AU2014281549B2 (ko) |
| BR (1) | BR112015031653A2 (ko) |
| CA (1) | CA2914135C (ko) |
| ES (1) | ES2659759T3 (ko) |
| MX (1) | MX367343B (ko) |
| PL (1) | PL3010946T3 (ko) |
| WO (1) | WO2014205084A1 (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3478758A2 (en) * | 2016-06-29 | 2019-05-08 | Holland Novochem Technical Coatings B.V. | Catalytically active radical scavengers based on benzylic and allylic functionalities |
| US11253625B2 (en) | 2018-06-27 | 2022-02-22 | Bausch & Lomb Incorporated | Ophthalmic device packaging solutions comprising a poloxamine/erythritol mixture |
| CN111285845B (zh) * | 2020-02-11 | 2021-01-01 | 深圳厚存纳米药业有限公司 | 末端官能团化的泊洛沙胺衍生物 |
| BR112023002449A2 (pt) | 2020-08-10 | 2023-03-28 | Bausch Lomb Ireland Ltd | Soluções de embalagem |
| AU2022231886A1 (en) | 2021-03-10 | 2023-09-14 | Bausch + Lomb Ireland Limited | Contact lens treating solution |
| US12012238B2 (en) | 2021-05-26 | 2024-06-18 | Bausch + Lomb Ireland Limited | Packaging solutions |
| CN115616096A (zh) * | 2021-07-16 | 2023-01-17 | 张家港市国泰华荣化工新材料有限公司 | 有机硅产品中bht和mehq的测定方法 |
| US20230159202A1 (en) | 2021-11-23 | 2023-05-25 | Bausch + Lomb Ireland Limited | Method for making a preservative-free packaged ophthalmic device product |
| US20230266505A1 (en) | 2022-02-24 | 2023-08-24 | Bausch + Lomb Ireland Limited | Ophthalmic devices |
| CN114948795B (zh) * | 2022-07-08 | 2023-09-08 | 上海信悉智能技术有限公司 | 一种温敏感凝胶面膜液及其制备方法 |
| US20240166971A1 (en) | 2022-10-26 | 2024-05-23 | Bausch + Lomb Ireland Limited | Contact lens treating solution |
| US20240218291A1 (en) | 2022-12-22 | 2024-07-04 | Bausch + Lomb Ireland Limited | Contact lens treating solution |
| US20240317988A1 (en) | 2023-03-22 | 2024-09-26 | Bausch + Lomb Ireland Limited | Monofunctional silicone monomers and silicone hydrogels formed therefrom |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000007603A2 (en) | 1998-08-04 | 2000-02-17 | Madash Llp | End modified thermal responsive hydrogels |
| US6517933B1 (en) | 2000-01-18 | 2003-02-11 | Nano-Tex, Llc | Hybrid polymer materials |
| CA2440844A1 (en) | 2001-03-20 | 2002-09-26 | Universitat Zurich | Two-phase processing of thermosensitive polymers for use as biomaterials |
| JP2002296774A (ja) * | 2001-03-30 | 2002-10-09 | Fuji Photo Film Co Ltd | 平版印刷版用原版 |
| EP1516009A1 (de) * | 2002-06-11 | 2005-03-23 | Basf Aktiengesellschaft | (meth)acrylester von polyalkoxyliertem trimethylolpropan |
| US8197841B2 (en) * | 2004-12-22 | 2012-06-12 | Bausch & Lomb Incorporated | Polymerizable surfactants and their use as device forming comonomers |
| DE102006049803A1 (de) * | 2006-10-23 | 2008-04-30 | Clariant International Limited | Hydroxyfunktionelle, copolymerisierbare Polyalkylenglykol-Makromonomere, deren Herstellung und Verwendung |
| WO2009073374A2 (en) * | 2007-12-03 | 2009-06-11 | Bausch & Lomb Incorporated | Method for inhibiting attachment of microorganisms to biomedical devices |
| US8293838B2 (en) | 2008-06-20 | 2012-10-23 | Adhezion Biomedical, Llc | Stable and sterile tissue adhesive composition with a controlled high viscosity |
| JP2013204001A (ja) * | 2012-03-29 | 2013-10-07 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性樹脂組成物およびそれを用いた積層体 |
-
2014
- 2014-06-18 CA CA2914135A patent/CA2914135C/en active Active
- 2014-06-18 US US14/308,229 patent/US9309357B2/en active Active
- 2014-06-18 PL PL14737465T patent/PL3010946T3/pl unknown
- 2014-06-18 MX MX2015016562A patent/MX367343B/es active IP Right Grant
- 2014-06-18 KR KR1020167000830A patent/KR101767852B1/ko active IP Right Grant
- 2014-06-18 ES ES14737465.6T patent/ES2659759T3/es active Active
- 2014-06-18 AU AU2014281549A patent/AU2014281549B2/en active Active
- 2014-06-18 JP JP2016521543A patent/JP6159025B2/ja active Active
- 2014-06-18 CN CN201480034803.7A patent/CN105308080B/zh active Active
- 2014-06-18 EP EP14737465.6A patent/EP3010946B1/en active Active
- 2014-06-18 WO PCT/US2014/042951 patent/WO2014205084A1/en active Application Filing
- 2014-06-18 BR BR112015031653A patent/BR112015031653A2/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| CA2914135C (en) | 2017-11-14 |
| CN105308080B (zh) | 2017-06-09 |
| CN105308080A (zh) | 2016-02-03 |
| EP3010946A1 (en) | 2016-04-27 |
| US9309357B2 (en) | 2016-04-12 |
| AU2014281549B2 (en) | 2017-02-02 |
| JP2016524014A (ja) | 2016-08-12 |
| US20140371481A1 (en) | 2014-12-18 |
| KR101767852B1 (ko) | 2017-08-11 |
| PL3010946T3 (pl) | 2018-06-29 |
| CA2914135A1 (en) | 2014-12-24 |
| MX367343B (es) | 2019-08-15 |
| MX2015016562A (es) | 2016-03-31 |
| BR112015031653A2 (pt) | 2017-07-25 |
| WO2014205084A1 (en) | 2014-12-24 |
| AU2014281549A1 (en) | 2016-01-07 |
| EP3010946B1 (en) | 2017-12-20 |
| KR20160019536A (ko) | 2016-02-19 |
| ES2659759T3 (es) | 2018-03-19 |
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